2-Nitrofluorene
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This review is focused on genotoxic 2-nitrofluorene, which is a marker for the presence of nitrated polycyclic aromatic hydrocarbons, and summarizes the current knowledge about the negative effects of 2-nitrofluorene and its metabolites on living organisms, especially on their DNA. These findings obtained via in vivo investigations are compared with information obtained using electrochemical DNA biosensors, which represent very promising in vitro alternative to the study of processes proceeding in living organisms during the interaction of their DNA with various xenobiotic compounds.
- Klíčová slova
- DNA biosenzory,
- MeSH
- elektrochemické techniky metody využití MeSH
- lidé MeSH
- polycyklické aromatické uhlovodíky * škodlivé účinky MeSH
- poškození DNA * MeSH
- xenobiotika metabolismus MeSH
- znečištění životního prostředí MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- práce podpořená grantem MeSH
In this paper we investigated the ability of 2-nitrofluorene to induce mutations leading to antibiotic resistance in quinolone-sensitive strain Salmonella typhimurium. After preincubation of bacteria with 2-nitrofluorene, the frequency of mutation to ciprofloxacin resistance was 57 fold higher than in the case of spontaneous mutability. Some of resultant resistant colonies showed a great increase of ciprofloxacin MIC.
- MeSH
- antiinfekční látky farmakologie MeSH
- bakteriální geny účinky léků MeSH
- bakteriální léková rezistence genetika MeSH
- ciprofloxacin farmakologie MeSH
- fluoreny farmakologie MeSH
- mutace účinky léků MeSH
- Salmonella typhimurium účinky léků genetika MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The interaction of genotoxic environmental pollutant 2-nitrofluorene (2-NF) with double-stranded DNA has been studied using a hanging mercury drop electrode (HMDE) as an electrochemical sensor. Two types of DNA damage were investigated and electrochemically detected using cyclic voltammetry and differential pulse voltammetry: (i) DNA damage caused by the direct interaction with 2-NF and (ii) DNA damage caused by short-lived radicals generated by the electrochemical reduction of 2-NF. For the study of the direct interaction, the HMDE was modified by DNA and the interaction of DNA with 2-NF was studied after their mutual interaction right at the HMDE surface, or DNA was preincubated with 2-NF in solution and, subsequently, the interaction was studied voltammetrically. Using both detection techniques, the formation of DNA-2-NF complex was observed and the mutual interaction was interpreted as an intercalation between DNA base pairs. On the basis of obtained results, we suppose that expected formation of 8-oxoguanosine leads to guanosine-cytidine base pair interruption and DNA double-strand break formation. The binding constants (K) of the DNA-2-NF complex formed in solution and on the HMDE surface (DNA/HMDE) were determined from the changes in the voltammetric peaks of the studied analyte.
- MeSH
- DNA * metabolismus MeSH
- elektrody MeSH
- fluoreny MeSH
- poškození DNA MeSH
- rtuť * MeSH
- Publikační typ
- časopisecké články MeSH
An electrochemical DNA biosensor based on the screen printed carbon paste electrode (SPCPE) with an immobilized layer of calf thymus double-stranded DNA has been used for in vitro investigation of the interaction between genotoxic nitro derivatives of fluorene (namely 2-nitrofluorene and 2,7-dinitrofluorene) and DNA. Two types of DNA damage have been detected at the DNA/SPCPE biosensor: first, that caused by direct association of the nitrofluorenes, for which an intercalation association has been found using the known DNA intercalators [Cu(phen)(2)](2+) and [Co(phen)(3)](3+) as competing agents, and, second, that caused by short-lived radicals generated by electrochemical reduction of the nitro group (observable under specific conditions only).
AIM: The purpose of this study was to determine how various compounds known to be positive mutagens, contribute to the development of mutations leading to ciprofloxacin resistance in Salmonella enterica subsp. enterica serotype Typhimurium. The molecular mechanism of ciprofloxacin resistance in treated strains was investigated. METHODS: A modified version of the incorporation plate test was used for quantitative determination of ciprofloxacin resistant mutants and for assessment of the mutation frequency induced by the positive mutagens in different concentrations. An AS-PCR-RFLP for monitoring of gyrA mutations was applied. RESULTS: Mutation frequency, expressed as number of antibiotic resistant colonies per 10(8) viable cells, was much higher after exposure of bacterial cells to 3-(5-nitro-2-furyl) acrylic acid and 2-nitrofluorene. All isolated cultures retain decreased susceptibility to antibiotic after multiple passages in antibiotic-free medium. 2-nitrofluorene was the best inducer of mutations in gyrA and in regulation genes affecting suppression of synthesis of outer membrane porins. 3-(5-nitro-2-furyl) acrylic acid gives rise to overproduction of efflux pump. CONCLUSIONS: The data suggest that antibiotic resistance may not be only a consequence of misuse of antibiotics. A polluted environment as well as food processing could contribute to this unwanted process.
- MeSH
- akryláty farmakologie MeSH
- antibakteriální látky farmakologie MeSH
- bakteriální léková rezistence genetika MeSH
- bakteriální proteiny genetika MeSH
- ciprofloxacin farmakologie MeSH
- DNA gyráza genetika MeSH
- fluoreny farmakologie MeSH
- látky znečišťující vzduch farmakologie MeSH
- mikrobiální testy citlivosti MeSH
- mutace účinky léků MeSH
- mutační rychlost MeSH
- mutageny farmakologie MeSH
- nitrofurany farmakologie MeSH
- poriny biosyntéza MeSH
- proteiny vnější bakteriální membrány biosyntéza MeSH
- regulace genové exprese u bakterií MeSH
- Salmonella typhimurium účinky léků genetika MeSH
- Publikační typ
- časopisecké články MeSH
Genotoxic nitrated polycyclic aromatic hydrocarbons (NPAHs) are formed during incomplete combustion processes by reaction of polycyclic aromatic hydrocarbons (PAHs) with atmospheric nitrogen oxides. 1-Nitropyrene, 2-nitrofluorene, and 3-nitrofluoranthene as the dominating substances are used as markers of NPAHs formation by these processes. In the presented study, voltammetric properties and quantification of these compounds and of 5-nitroquinoline (as a representative of environmentally important genotoxic heterocyclic compounds) have been investigated using a mercury meniscus modified silver solid amalgam electrode (m-AgSAE), which represent a nontoxic alternative to traditional mercury electrodes. Linear calibration curves over three orders of magnitude and limits of determination mostly in the 10(-7) mol L(-1) concentration range were obtained using direct current and differential pulse voltammetry. Further, satisfactory HPLC separation of studied analytes in fifteen minutes was achieved using 0.01 mol L(-1) phosphate buffer, pH 7.0 : methanol (15 : 85, v/v) mobile phase, and C(18) reversed stationary phase. Limits of detection of around 1 · 10(-5) mol L(-1) were achieved using amperometric detection at m-AgSAE in wall-jet arrangement for all studied analytes. Practical applicability of this technique was demonstrated on the determination of 1-nitropyrene, 2-nitrofluorene, 3-nitrofluoranthene, and 5-nitroquinoline in drinking water after their preliminary separation and preconcentration using solid phase extraction with the limits of detection around 1 · 10(-6) mol L(-1).
